CN100341872C - 用作植物杀真菌剂的吡啶并二嗪 - Google Patents
用作植物杀真菌剂的吡啶并二嗪 Download PDFInfo
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- CN100341872C CN100341872C CNB2003801073989A CN200380107398A CN100341872C CN 100341872 C CN100341872 C CN 100341872C CN B2003801073989 A CNB2003801073989 A CN B2003801073989A CN 200380107398 A CN200380107398 A CN 200380107398A CN 100341872 C CN100341872 C CN 100341872C
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- alkyl
- alkoxyl group
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- halogen
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- OHZYAOYVLLHTGW-UHFFFAOYSA-N pyrido[3,2-c]pyridazine Chemical class C1=CN=NC2=CC=CN=C21 OHZYAOYVLLHTGW-UHFFFAOYSA-N 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 702
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 10
- -1 heteroaryl sulfenyl Chemical group 0.000 claims description 332
- 125000000217 alkyl group Chemical group 0.000 claims description 212
- 125000005843 halogen group Chemical group 0.000 claims description 121
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 94
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 239000000203 mixture Substances 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 82
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 229910052731 fluorine Inorganic materials 0.000 claims description 52
- 239000011737 fluorine Chemical group 0.000 claims description 51
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 44
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 44
- 239000000460 chlorine Substances 0.000 claims description 41
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 229910052727 yttrium Inorganic materials 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
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- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
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- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical class 0.000 claims description 4
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 239000013461 intermediate chemical Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical class N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
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- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 208000011079 pinta disease Diseases 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CPAUHNHNGALXSY-UHFFFAOYSA-N propan-2-yl n-butylcarbamate Chemical compound CCCCNC(=O)OC(C)C CPAUHNHNGALXSY-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- BEJXOECDIXUTLN-UHFFFAOYSA-N pyrido[2,3-c]pyridazine Chemical compound N1=NC=CC2=CC=CN=C21 BEJXOECDIXUTLN-UHFFFAOYSA-N 0.000 description 1
- GIVUQTUKKWDKHE-UHFFFAOYSA-N pyrido[2,3-d]pyridazine Chemical compound C1=NN=CC2=CC=CN=C21 GIVUQTUKKWDKHE-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0230020.0A GB0230020D0 (en) | 2002-12-23 | 2002-12-23 | Fungicides |
| GB0230020.0 | 2002-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1732168A CN1732168A (zh) | 2006-02-08 |
| CN100341872C true CN100341872C (zh) | 2007-10-10 |
Family
ID=9950323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2003801073989A Expired - Fee Related CN100341872C (zh) | 2002-12-23 | 2003-12-03 | 用作植物杀真菌剂的吡啶并二嗪 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7410967B2 (es) |
| EP (1) | EP1575948B1 (es) |
| JP (1) | JP4847017B2 (es) |
| KR (1) | KR101099434B1 (es) |
| CN (1) | CN100341872C (es) |
| AR (1) | AR042660A1 (es) |
| AT (1) | ATE353897T1 (es) |
| AU (1) | AU2003288410B2 (es) |
| BR (1) | BR0317678A (es) |
| CA (1) | CA2509451C (es) |
| CR (1) | CR7864A (es) |
| DE (1) | DE60311876T2 (es) |
| DK (1) | DK1575948T3 (es) |
| EC (1) | ECSP055863A (es) |
| ES (1) | ES2282702T3 (es) |
| GB (1) | GB0230020D0 (es) |
| GT (1) | GT200300298A (es) |
| IL (1) | IL169186A (es) |
| MX (1) | MXPA05006648A (es) |
| PT (1) | PT1575948E (es) |
| RU (1) | RU2352570C2 (es) |
| TW (1) | TWI326683B (es) |
| WO (1) | WO2004056825A1 (es) |
| ZA (1) | ZA200504296B (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0230018D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230020D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| DK1599468T3 (da) | 2003-01-14 | 2008-02-04 | Arena Pharm Inc | 1,2,3-trisubstituerede aryl- og heteroarylderivater som modulatorer af metabolisme og forebyggelse og behandling af forstyrrelser forbundet dermed såsom diabetes og hyperglykæmi |
| WO2005010000A2 (de) * | 2003-07-18 | 2005-02-03 | Basf Aktiengesellschaft | Arylkondensierte 3-arylpyridinverbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| GB0413955D0 (en) * | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| GB0413953D0 (en) * | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| WO2007088060A1 (en) * | 2006-02-03 | 2007-08-09 | Syngenta Participations Ag | Tetrahydropyrido [2, 3-b] pyrazine and dihydropyrido [2 , 3-b] pyrazine derivatives as plant fungicides |
| GB0614471D0 (en) | 2006-07-20 | 2006-08-30 | Syngenta Ltd | Herbicidal Compounds |
| EP1920654A1 (en) | 2006-09-13 | 2008-05-14 | Syngeta Participations AG | Novel pyridopyrazine N-oxides |
| US20100093738A1 (en) * | 2006-10-06 | 2010-04-15 | Basf Se | Fungicidal Compounds and Fungicidal Compositions |
| GB0624760D0 (en) * | 2006-12-12 | 2007-01-17 | Syngenta Ltd | Herbicidal compounds |
| GB0800855D0 (en) | 2008-01-17 | 2008-02-27 | Syngenta Ltd | Herbicidal compounds |
| GB0800856D0 (en) | 2008-01-17 | 2008-02-27 | Syngenta Ltd | Herbicidal compounds |
| SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| CN102273441B (zh) * | 2011-09-13 | 2015-01-07 | 广西田园生化股份有限公司 | 含嘧菌酯的超低容量液剂 |
| CN102273442A (zh) * | 2011-09-13 | 2011-12-14 | 广西田园生化股份有限公司 | 含氟环唑的超低容量液剂 |
| EP3242666A1 (en) | 2015-01-06 | 2017-11-15 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１Ｐ１レセプター関連障害における使用のための（Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸（化合物１）の結晶性Ｌ−アルギニン塩 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5821244A (en) * | 1993-03-13 | 1998-10-13 | Hoechst Schering Agrevo Gmbh | Condensed nitrogen heterocycles and their use as pesticides, fungicides and antimycotics |
| EP1249452A1 (en) * | 2001-04-09 | 2002-10-16 | Basf Aktiengesellschaft | Fungicidal 5-Alkylamino-6-phenyl-7-halo-triazolopyrimidines |
| WO2002083676A1 (en) * | 2001-04-11 | 2002-10-24 | Basf Aktiengesellschaft | 5-halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1004223A (en) | 1972-05-12 | 1977-01-25 | Theodor Denzel | Amino derivatives of pyrido(2,3-d)pyridazine carboxylic acids and esters |
| US3984412A (en) | 1974-07-25 | 1976-10-05 | E. R. Squibb & Sons, Inc. | Amino derivatives of pyrido[2,3-b]pyrazine carboxylic acids and esters |
| DE3644825A1 (de) | 1986-12-31 | 1988-07-14 | Basf Ag | Substituierte 1,8-naphthyridin-derivate und diese enthaltende fungizide |
| US5258356A (en) | 1989-03-11 | 1993-11-02 | Basf Aktiengesellschaft | Substituted 1,8-naphthyridines, their preparation and their use as antidotes |
| AU634561B2 (en) | 1989-07-27 | 1993-02-25 | Eli Lilly And Company | Naphthyridine derivatives |
| DE4131029A1 (de) | 1991-09-18 | 1993-07-29 | Basf Ag | Substituierte pyrido (2,3-d) pyrimidine als antidots |
| DE4434637A1 (de) | 1994-09-28 | 1996-04-04 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
| AU6987096A (en) | 1995-09-12 | 1997-04-01 | Basf Aktiengesellschaft | Fungicidal quinolines |
| GB2323476B (en) * | 1997-03-20 | 2002-01-16 | David Ganeshmoorthy | Communication antenna and equipment |
| US6117884A (en) | 1997-07-31 | 2000-09-12 | Daeuble; John | 4-substituted quinoline derivatives having fungicidal activity |
| PT1210333E (pt) | 1999-09-07 | 2005-03-31 | Syngenta Participations Ag | P-tolil-heterociclos como herbicidas |
| JP2002249492A (ja) | 2000-12-22 | 2002-09-06 | Nippon Bayer Agrochem Co Ltd | トリアゾロピリミジン類 |
| ATE274518T1 (de) | 2001-04-11 | 2004-09-15 | Basf Ag | 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine |
| DE10121102A1 (de) | 2001-04-27 | 2002-11-07 | Bayer Ag | Triazolopyrimidine |
| DE10121101A1 (de) | 2001-04-27 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10121162A1 (de) | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| GB0230021D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230018D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230020D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230019D0 (en) | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
-
2002
- 2002-12-23 GB GBGB0230020.0A patent/GB0230020D0/en not_active Ceased
-
2003
- 2003-12-03 WO PCT/GB2003/005250 patent/WO2004056825A1/en active IP Right Grant
- 2003-12-03 KR KR1020057011805A patent/KR101099434B1/ko not_active IP Right Cessation
- 2003-12-03 BR BR0317678-9A patent/BR0317678A/pt not_active Application Discontinuation
- 2003-12-03 ES ES03780329T patent/ES2282702T3/es not_active Expired - Lifetime
- 2003-12-03 RU RU2005123331/04A patent/RU2352570C2/ru not_active IP Right Cessation
- 2003-12-03 PT PT03780329T patent/PT1575948E/pt unknown
- 2003-12-03 DK DK03780329T patent/DK1575948T3/da active
- 2003-12-03 CA CA2509451A patent/CA2509451C/en not_active Expired - Fee Related
- 2003-12-03 DE DE60311876T patent/DE60311876T2/de not_active Expired - Lifetime
- 2003-12-03 CN CNB2003801073989A patent/CN100341872C/zh not_active Expired - Fee Related
- 2003-12-03 AT AT03780329T patent/ATE353897T1/de active
- 2003-12-03 US US10/540,035 patent/US7410967B2/en not_active Expired - Fee Related
- 2003-12-03 EP EP03780329A patent/EP1575948B1/en not_active Expired - Lifetime
- 2003-12-03 JP JP2004561603A patent/JP4847017B2/ja not_active Expired - Fee Related
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- 2003-12-22 AR ARP030104799A patent/AR042660A1/es unknown
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- 2003-12-23 TW TW092136597A patent/TWI326683B/zh not_active IP Right Cessation
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2005
- 2005-05-26 ZA ZA200504296A patent/ZA200504296B/en unknown
- 2005-06-07 CR CR7864A patent/CR7864A/es not_active Application Discontinuation
- 2005-06-15 IL IL169186A patent/IL169186A/en not_active IP Right Cessation
- 2005-06-17 EC EC2005005863A patent/ECSP055863A/es unknown
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2008
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5821244A (en) * | 1993-03-13 | 1998-10-13 | Hoechst Schering Agrevo Gmbh | Condensed nitrogen heterocycles and their use as pesticides, fungicides and antimycotics |
| EP1249452A1 (en) * | 2001-04-09 | 2002-10-16 | Basf Aktiengesellschaft | Fungicidal 5-Alkylamino-6-phenyl-7-halo-triazolopyrimidines |
| WO2002083676A1 (en) * | 2001-04-11 | 2002-10-24 | Basf Aktiengesellschaft | 5-halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides |
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